Photocleavable Ortho-Nitrobenzyl-Protected DNA Architectures and Their Applications
Chemical Reviews,
Год журнала:
2023,
Номер
123(10), С. 6839 - 6887
Опубликована: Апрель 20, 2023
This
review
article
introduces
mechanistic
aspects
and
applications
of
photochemically
deprotected
Язык: Английский
Oligonucleotides: evolution and innovation
Medicinal Chemistry Research,
Год журнала:
2024,
Номер
unknown
Опубликована: Ноя. 21, 2024
Abstract
Oligonucleotides,
comprising
single
or
double
strands
of
RNA
DNA,
are
vital
chemical
compounds
used
in
various
laboratory
and
clinical
applications.
They
represent
a
significant
class
therapeutics
with
rapidly
expanding
range
uses.
Between
1998
2023,
19
oligonucleotides
have
received
approval
from
the
U.S.
Food
Drug
Administration
(FDA).
Their
synthesis
methods
undergone
evolution
over
time.
This
review
examines
several
oligonucleotide
techniques,
including
phosphodiester,
phosphotriester,
phosphoramidite
approaches.
It
begins
discussion
an
early
method
involving
phosphoryl
chloride
intermediate,
which
proved
unstable
prone
to
hydrolysis.
The
then
transitions
solid-phase
method,
uses
polymer
resins
as
solid
support,
emphasizing
its
advantages
both
phosphotriester
techniques.
is
followed
by
exploration
recent
advancements
enzymatic
synthesis,
concluding
on
modifications
bases,
sugars,
backbones
designed
improve
their
properties
therapeutic
potential.
Язык: Английский
The effect of neighbouring group participation and possible long range remote group participation in O-glycosylation
Beilstein Journal of Organic Chemistry,
Год журнала:
2025,
Номер
21, С. 369 - 406
Опубликована: Фев. 17, 2025
Stereoselective
glycosylations
are
one
of
the
most
challenging
tasks
synthetic
glycochemists.
The
protecting
building
blocks
on
glycosides
contribute
significantly
in
attaining
required
stereochemistry
resulting
glycosides.
Strategic
installation
suitable
groups
C-2
position,
vicinal
to
anomeric
carbon,
renders
neighbouring
group
participation,
whereas
distal
C-3,
C-4,
and
C-6
positions
often
claimed
exhibit
remote
participation
with
carbon.
Neighbouring
being
widely
studied
help
glycochemists
design
protocols
for
multistep
synthesis
complex
oligosaccharides
turn,
standardise
process
glycosylation
towards
a
particular
stereochemical
output.
While
has
been
quite
effective
achieving
produced
glycosides,
exhibits
comparatively
less
efficacy
complete
stereoselectivity
reactions.
Remote
is
still
highly
debated
topic
scientific
community.
However,
implementing
participating
role
reactions
practised
achieve
better
stereocontrol
facilitate
formation
synthetically
glycosidic
linkages.
Язык: Английский
Photolabile ortho‐Nitro‐Benzyl Carbonate as a Permanent Hydroxyl Protecting Group for the Synthesis of Digalactosyl Diacylglycerol
Chinese Journal of Chemistry,
Год журнала:
2024,
Номер
unknown
Опубликована: Окт. 16, 2024
Comprehensive
Summary
Traditional
protecting
groups
are
often
removed
under
harsh
conditions
with
potentially
hazardous
reagents,
thereby
impeding
the
convenient
synthesis
of
oligosaccharides
and
glycosides.
Herein,
we
present
to
utilize
photolabile
ortho
‐nitro‐benzyl
carbonate
(
o
NBC)
as
a
permanent
hydroxyl
group
for
stereocontrolled
The
Ph
3
PO‐modulated
glycosylation
strongly
disarmed
per‐
O
‐
NBC‐protected
glycosyl
ynenoates
preferred
afford
glycosides
excellent
α‐selectivities
via
β‐phosphonium
transition
state.
Based
on
NBC‐mediated
galactosylation,
glycolipid
digalactosyl
diacylglycerol
(DGDG)
containing
six
double
bonds
two
esters
was
achieved
in
straightforward
manner.
Язык: Английский
Photo-labile BODIPY protecting groups for glycan synthesis
Chemical Communications,
Год журнала:
2022,
Номер
58(75), С. 10556 - 10559
Опубликована: Янв. 1, 2022
Protective
groups
that
can
be
selectively
removed
under
mild
conditions
are
an
essential
aspect
of
carbohydrate
chemistry.
Groups
by
visible
light
particularly
attractive
because
carbohydrates
transparent
to
light.
Here,
different
BODIPY
protecting
were
explored
for
their
utility
during
glycan
synthesis.
A
group
bearing
a
boron
difluoride
unit
is
stable
glycosylations
but
cleaved
with
green
as
illustrated
the
assembly
trisaccharide.
Язык: Английский
Orthogonal Deprotection of Photolabile Protecting Groups and Its Application in Oligosaccharide Synthesis
Organic Letters,
Год журнала:
2024,
Номер
26(27), С. 5746 - 5751
Опубликована: Июль 2, 2024
We
herein
report
for
the
first
time
inter-
and
intramolecular
orthogonal
cleavage
of
two
Язык: Английский
C2‐Cyanomethyl (CNMe) Ether‐Protected Glycosyl Trichloroacetimidate Donors for Stereoselective β‐O‐Glycosylations
European Journal of Organic Chemistry,
Год журнала:
2023,
Номер
26(15)
Опубликована: Март 1, 2023
Abstract
Stereoselective
construction
of
glycosidic
linkages
have
emerged
as
one
the
pivotal
aspects
for
synthesis
complex
oligosaccharide
assemblies.
We
herein
report
C2‐cyanomethyl
(CNMe)
ether
a
strong
stereodirecting
group
on
trichloroacetimidate
glycosyl
donors
1,2‐
trans
‐β‐
O
‐glycosides.
The
developed
bearing
various
arming
and
disarming
protections
along
with
C2‐CNMe
delivered
glycosides
in
short
reaction
time,
moderate
to
good
yields
high
excellent
stereoselectivities.
Gluco
‐
galacto
configured
were
found
compatible
an
array
alcohols
having
varied
reactivities.
orthogonality
CNMe
protection
silyl
has
been
further
explored
sequential
glycosylations.
Язык: Английский
Photosensitive Fluorous Tag-Assisted Convergent Synthesis of β-1,4-Mannuronates
Organic Letters,
Год журнала:
2023,
Номер
25(19), С. 3548 - 3552
Опубликована: Май 9, 2023
Rapid
synthesis
of
saccharides
by
a
chemical
method
is
an
efficient
way
to
meet
the
demand
for
well-defined
glycans
probe
their
biological
functions.
Herein,
feasible
and
convenient
strategy
saccharide
was
established
introducing
photosensitive
fluorous
tag
at
anomeric
position
glycosides.
The
used
not
only
in
polytetrafluoroethylene-assisted
rapid
purification
but
also
as
temporary
protecting
group
reducing
end
carbohydrates.
tag-protected
glycosides
could
be
transformed
into
new
glycosyl
donors
convergent
after
orthogonal
deprotection
photolysis.
Via
combination
β-directing
C-5
carboxylate
glycosylation
strategy,
β-1,4-mannuronates
were
efficiently
prepared.
Язык: Английский
1,4-Naphthoquinone Derivative as Efficient Photolabile Molecule: Concise Synthesis and Photorelease of Various Functional Compounds
Synthesis,
Год журнала:
2022,
Номер
55(01), С. 150 - 158
Опубликована: Авг. 29, 2022
Abstract
We
report
on
a
series
of
1,4-naphthoquinone
(NQ)-based
photolabile
molecules,
including
various
functional
compounds
to
be
released
under
light
irradiation.
They
were
efficiently
prepared
from
common
precursor
for
photoremovable
masking
group,
by
attaching
different
such
as
alcohols,
amines,
and
acids
concise
synthetic
method.
Synthesis
the
was
optimized
two-step
reactions
also
one-pot
reaction
involving
1,4-addition
successive
aldol
NQ.
The
compounds,
amines
carboxylic,
phosphoric,
sulfonic
acids,
masked
with
NQ-based
successfully
irradiation
UV
(λ
=
360
nm)
in
high
yields
(>90%).
Язык: Английский